Azo dyestuff



Patented Aug. 7, 1934 a i UNITE'DYSTATES AZQ DYESTUFF Karl Holzach, Ludwigshafen-onthe-lthine, and Guido von Rosenberg, Mannheim Germany,

" assignors to General Aniline Works, 1m, New York, N.-Y.,'a;'corp oration of-Delaware No Drawing l Application July 1,1929, Serial Germany July 5, 1928 Renewed December 7, 1933. I11- 6 Claims. (d1. 26046) The present invention relates to the production of azo dyestuffs containing 4-hydroxyquinolones as coupling components.

. We have foundthat valuable azo dyestuffs are 5 obtained by coupling diazo compounds free from sulphonic and carboxylic acid groups with quinolones also free from the saidgroups correspondlng to the general formula:

in which R. stands for an alkyl, aralkyl or a cyclic radicle which may be substituted and Y for hydrogen or any substituent other than the sulfonic and carboxylic acidgroups.

The new products are insoluble in water, and can be employed as pigment dyestuffs or for dyeing acetate silk, a large number of them have ing an extremely good affinity for acetate silk. For example, dyestuffs are obtained by coupling the diazo compounds of aniline or its homologues with N-methyl-4-hydroxy-2-quinolone, which give dyeings on acetate silk having valuable greenish yellow shades and excellent fastness properties, and which are also suitable for printing on acetate silk.; I

The shade of the dyestufi obtained can be varied within wide limits by appropriate choice of the diazo or coupling component employed. The azo dyestuffs obtained, when employing N- alkyl-4-hydroxyquinolone as coupling component, are of great value, in particular those obtainable from diaz otized m-nitraniline. v The following examples will further illustrate the nature of the said invention, but thei'nve'ntion is not restricted to these examples. The parts are by weight. V l

Example 1 A diazo solution prepared the usual manner from 6.2 parts of aniline is'allowed to run at a. temperature between 0 and C into a $0111 filtered off by suction. The dyestufi corresponding to -'th'e formula:

is a yellow powder which when triturated with the usual substrata, forms apigment of good fastness properties. The preparation can also be carried out from the beginning in the presence of substrata.

Example 2 H on H; No,

which separates out is filtered off by suction. It gives a strong, very fast, greenish yellow dyeing on acetate silk from a suspension in water with the usual additions.

Example 3 A diazo solution prepared in the'usual manner from 12.8 parts of p-chloraniline is allowed to run at atemperature of about 10 G. into a solution of 21.5 parts of 6-chlor-N-ethyl-4-hydroxy-2- quinolone (obtainable by heating '5-chlor-2- ethylamino-l-benzoic acid with aceticuacid anhydride) in 500 parts of a 2.2 per cent sodium Y carbonate solution to which 15 parts of sodium bicarbonate have been added and the whole is stirred at about 10 C. until the diazo compound is used up. The dyestuff corresponding to the which separates out is filtered ofi by suction. It gives a strong, very fast, yellow dyeing on acetate silk from an aqueous suspension with the usual additions.

Example 4 A diazo solution prepared in the usual manner from 13.6 parts of p-aminodimethylaniline is allowed to run :at a temperature betweenabout zero and 5 G. into a solution of 17.5 parts of N-methyl- 4-hydroxy-2-quino1one and 20 parts of soda in 500 parts of water. The reaction mixture is stirred until the d'iazo compound is used up. The insoluble dyestuff formed corresponding to the formula:

is filtered by suction and is a violet brown powder when dried. It has a good afiinity to acetate silk which is dyed violet shades from its aqueous suspension.

Example 5 A diazo solution prepared in the usual manner from 13. 8 parts of m-mtrtaniline are run at a temperature of about :zero into a solution of .27 parts of xN-(.2"-methoxypl'ienyl) -4-hydroxy-2- quin'ol'one (obtainable by :heating N 2 methoxyphenylwanthranilic acid with acetic acid anhydride) and 30 .parts of soda in 500 parts of water. .After the 'diazo compound :has been consumedzthezdyestufi corresponding tothe formula:

OCH

prising as coupling component a quinolone corresponding to the general formula:

Y i in which R. stands for an alkyl, aralkyl or cyclic radicle, and Y for hydrogen or halogen.

2. .Azo dyestuffs free from acid groups comprising as coupling component a quinolone corresponding to the formula:

H OH

in which R stands for an alkyl group.

'3. The azo 'dyestufis corresponding to the formula: i 00 N=N/\ N02 in which R stands for an alkyl group.

4. The azo dyest-mf corresponding to the r formula:

giving "a strong, very fast, greenish yellow -.dy-eing on :acetate silk.

5. Azo dyestuffs free from acid groups 'comprising as a coupling component a 'q-ui-nolone corresponding to the formula:

H on

Y 7 y 11; \g Ilq a wherein .R stands for .an alkyl group or a phenyl group :and Y stands for a hydrogen or halogen atom. f

.6. A10 dyestuffs corresponding .to the .general formula: 1'35 11 on 1 1 X group, Y stands for-a hydrogen or halogen atom, and .X stands for hydrogen, halogen, la nitro group or an amino -:group substituted lbytan alkyl KARL HQLZACH. 

